Real talk about starting a clothing company

I know a few things to be true: That many of you are interested in starting a clothing company, that the apparel business is hard as fuck, and that there is very, very little information out there on the actual tactics of building a brand or the day-to-day operations of running the business. There’s plenty of fluffy interviews with vague advice like “follow your passion,” but almost nothing about how to actually DO the shit it takes to get there: design the right product, build a brand, and convince people to actually give you their money.

I don’t have any experience working for a cool streetwear company, but I did spend about four years doing design and marketing for Abercrombie/Hollister a few years back when they were crushing it (I designed a few hundred Hollister girls shirts and spent months in Asian factories getting shit made), and I learned a lot about the business during those years – specifically, that anybody can put up a Shopify storefront and print up some t-shirts, but running a profitable apparel business is a totally different ballgame.

Which is why I was really stoked to stumble upon the Short Story Long podcast, hosted by Chris “Drama” Pfaff, the founder of the mall streetwear brand Young & Reckless – I was kind of expecting it to be douchey, but it’s actually a very, very good show about entrepreneurship. If you stopped listening there because you’re too cool for Y&R, then I suggest you put down your frosty mug of haterade – this podcast is GOLD for anyone who is interested in the apparel business. Losers hate, winners congratulate.

A few specific episodes I loved and suggest listening to:

Y&R co-founder Dee Murthy – some very real talk about the grind involved in getting a company off the ground and to the point of “ramen profitability.” A lot of sacrifice, risk and eating shit for years and years before you see any success at all…

Bobby Hundreds, founder of The Hundreds and So Cal hardcore kid. Again, maybe you hate The Hundreds but their success is no accident and there’s a lot to learn from it – Bobby is a sharp motherfucker and drops some serious knowledge here. I especially love the part where he and Chris talk about why they believe in selling their brands at the mall (in contrast to the many “too cool for school” brands who shit on it – and usually go out of business in 3 years)

Nick Diamond, founder of Diamond Supply Co. So many things to take note of in this convo, but in particular that the cornerstone of all his success is the network he built coming up in the legendary 90s Embarcadero/SF skateboarding scene – this is EXACTLY what I’m talking about when I say that the friends you’re making right now can and will end up being super valuable business partners years from now.

I actually didn’t know anything about Chris until I listened to this, but after binging on the show it’s no surprise to me that the brand blew up like it did – he is a very sharp, humble guy who is clearly super passionate about building a real business (not just making himself look cool, which is the #1 one priority for 90% of the mostly-shitty people in the apparel business). He’s also very busy and very rich, so it’s super cool of him to do this show and put so much energy into helping others build their own companies.

A few key takeaways in my (admittedly jaded) opinion:

It takes YEARS to build a brand. Not 1 or 2 years but 5, 7, 10 years.

It’s all about storytelling. Great product doesn’t sell itself – you need to be able to tell stories about the people and lifestyle that your brand is part of. Making the product is only step one. Don’t stop there.

You better LOVE this shit because it is going to get hard as fuck, and if you don’t love every minute of it you’re gonna quit.

If you understand technology you will have a big leg up on the competition – believe it or not, streetwear companies didn’t start embracing ecommerce until a couple years ago. They’re not exactly the most sophisticated people, so take advantage of that.

So there you go – if you have any interest in starting a clothing brand, do yourself a favor and listen to every episode of Short Story Long, take notes, and do what Chris and his friends say – this is the blueprint.